Inhibition of the [beta]-carbonic anhydrases from Mycobacterium tuberculosis with C-cinnamoyl glycosides: Identification of the first inhibitor with anti-mycobacterial activity

A small series of C-cinnamoyl glycoside containing the phenol moiety was tested for the inhibition of the three Mycobacterium tuberculosis [beta]-carbonic anhydrases (CAs, EC 4.2.1.1) with activities in the low micromolar range detected. The compounds were also tested for the inhibition of growth of...

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Bibliographic Details
Published in:Bioorganic & medicinal chemistry letters 2013-02, Vol.23 (3), p.740-743
Main Authors: Buchieri, Maria V, Riafrecha, Leonardo E, Rodriguez, Oscar M, Vullo, Daniela, Morbidoni, Hector R, Supuran, Claudiu T, Colinas, Pedro A
Format: Article
Language:English
Subjects:
Carbonate dehydratase
glycosides
Mycobacterium tuberculosis
Phenols
Tuberculosis
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Summary:A small series of C-cinnamoyl glycoside containing the phenol moiety was tested for the inhibition of the three Mycobacterium tuberculosis [beta]-carbonic anhydrases (CAs, EC 4.2.1.1) with activities in the low micromolar range detected. The compounds were also tested for the inhibition of growth of M. tuberculosis H37Rv strain, leading to the identification of (E)-1-(2a2,3a2,4a2,6a2-tetra-O-acetyl-[beta]-d-glucopyranosyl)- 4-(3-hydroxyphenyl)but-3-en-2-one (1) as the first carbonic anhydrase inhibitor with anti-tubercular activity.
ISSN:0960-894X